Hello, I am a guy and tend to have no problems once I know a woman is interested.  I have no problems making casual conversation, but I tend to over analyze the asking out part.  Most of my past relationships just happened naturally over time.  I am also a good communicator in a professional manner.  I talk to men and women all the time at work etc.

My social network is bad right now due to Real life issues of most of my friends, so I do not get out as Often as I should.

I see many women that I might be interested in, I just have a problem asking them out or whatever.  I do not want to come off like a womanizer and sort of have a fear of rejection I guess.

I am trying to get over this and come up with a good plan to start asking women out properly.  I almost feel like I am forcing it and it is awkward.

Say I see a nice girl at a shopping center, or gas station, even a cashier, I do not know how to approach them without it seeming sort of lame in my mind as I visualize they'd see it.  I don't want to come off as just another one of those guys who hits on every woman he sees.

Is it as simple as asking the girl if she would be interested in going out sometime?  then getting a telephone # etc?

This really should not be so complicated I know.  But any advice to make this easier is GREATLY appreciated.

If you ask a girl for her number, you're taking at least two risks: 1) that she has a boyfriend already; 2) that she doesn't want to give you her phone number, but she feels bad rejecting you so she gives it anyway hoping you really won't call.

Probably more often, she'll be glad to give her number to you, but if you're terrified of either of the above risks, I say...

Instead of asking for her number and creating a potentially uncomfortable moment of response on her part, I'd offer yourself to her.  Keep some business cards, or something creative about yourself with your phone number on it.  I'd also include an e-mail address or website, in case she has phone anxiety. It would be so sweet of you to approach her with respect to whatever her situation might be, in such a way that you might say...."Hey. I don't mean to look at you too much, but you seem like someone I'd like to talk to. In case you don't have a boyfriend, I'll give you my info, and please do not be shy. I'd love to hear from you." Then you can walk away. 

Well this is a bit tricky because most women are conditioned to be annoyed at guys who approach them but it is all because of the way some guys go about it. This has to do with a number of things. 1. The way that girls are approached is too forced and uncomfortable. 2. The guy uses pick up lines or ice breakers that are unoriginal making the girl feel just like any other girl And 3. The guys who often approach the girls assume that the girl cares about who you are. She does not know you so why should she care about what your name is and your agenda? Now at the same time, almost any woman would love to be approached by the right guy. A guy who is confident and original is very attractive. There needs to be a mystery about the guy that leaves the girl wanting more. This seems like a daunting task but it really is not.
The first thing you need to do is catch the girl off guard, be nice but not creepy. Smile but dont stare at her as if you are staring into her soul. And now for the words, this is very important. This is you trying to get her to care about what you are saying and leaving her interested in you in just a couple of sentences. If it is a girl you see all the time, this is easier because you can slowly ease your way in. But with girls that you see at malls or gas stations you only have one shot, so its clearly ok to be a little more forward. You need to have fun with it and dont act like it is the end of the world if you dont see her again. You want to get to know her but you dont know if shes worth dating, she may be an awful human being but you are taking the risk, just as she is. So you see a girl at the gas station, you are both pumping gas. You must think quickly. Try to get her to laugh to break the ice. Be original, be yourself. Then take the bold leap, tell her about a party or a bar, some event that sounds fun and tell her to bring her friends, this is less invasive. Give her the address of the party or bar, give her your number (although some girls even if they like a guy will not call), or take her number. It all depends on you and what you feel comfortable with. If you are going to act weird asking for her number she is going to feel weird giving it to you. In which case, just give the address of the place. If you ask for her number as if it is no big deal, saying something like, "oh yea its going to be a really good time, if you are down i can give you a call and let you know where it is?" If she says no, smile and say, "ok. well maybe see you there, and ...good luck with ______." ( a comment about the weather, something you had talked about etc) End it with showing the girl you are a nice guy who was listening to her.

you should not fear rejection, it is a part of life. And honestly this kind of rejection has little to do with what you look like or who you are. A girl that you just meet doesnt know you and girls go out with unattractive guys all the time, if a girl rejects you it is because you have not shown them that you are worth taking a risk for.